| Revision as of 19:58, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 462562684 of page Acetyldihydrocodeine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 23:41, 6 February 2024 edit VastV0idInSpace0 (talk | contribs)Extended confirmed users2,406 edits Fixed spacing between stub templates and category templates.Tag: 2017 wikitext editor |
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{{Short description|Opioid analgesic and cough suppressant drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Refimprove|date=November 2011}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 447732511 |
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| Watchedfields = changed |
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| IUPAC_name = 3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan |
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| verifiedrevid = 477240369 |
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| IUPAC_name = 3-methoxy-6-acetoxy-(5α,6α)-4,5-epoxy-17-methylmorphinan |
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| image = Acetyldihydrocodeine.svg |
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| image = Acetyldihydrocodeine.svg |
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| width = 200 |
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| width = 200 |
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| image2 = Acetyldihydrocodeine ball-and-stick.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| Drugs.com = {{drugs.com|international|acetyldihydrocodeine}} |
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| Drugs.com = {{drugs.com|international|acetyldihydrocodeine}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_AU = S8 (Controlled) |
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| legal_BR = A2 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-03 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_CA = Schedule I |
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| legal_UK = Class B |
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| legal_US = Schedule I |
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| legal_US = Schedule I |
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| legal_DE = Anlage I |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 3861-72-1 --> |
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| CAS_number = 3861-72-1 |
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| ATC_prefix = R05 |
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| ATC_prefix = R05 |
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| ATC_suffix = DA12 |
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| ATC_suffix = DA12 |
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| DrugBank = DB01538 |
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| DrugBank = DB01538 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 21106249 |
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| ChemSpiderID = 4576412 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = SGY1T84P34 |
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| UNII = SGY1T84P34 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=20 | H=25 | N=1 | O=4 |
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| C=20 | H=25 | N=1 | O=4 |
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| smiles = O=C(O45Oc1c2c(ccc1OC)C3N(CC253CC4)C)C |
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| molecular_weight = 343.417 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| smiles = CC(=O)O1CC5C2Cc4ccc(OC)c3O15(CC2C)c34 |
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| InChI = 1/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14?,16-,19-,20-/m0/s1 |
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| StdInChI = 1S/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| InChIKey = LGGDXXJAGWBUSL-PQSIUIEHBT |
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| StdInChIKey = LGGDXXJAGWBUSL-BKRJIHRRSA-N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14?,16-,19-,20-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LGGDXXJAGWBUSL-PQSIUIEHSA-N |
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| synonyms = Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine |
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| synonyms = Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine |
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}} |
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'''Acetyldihydrocodeine''' is an ] derivative discovered in Germany in 1914<ref>{{cite journal| vauthors = von Braun J |title = Untersuchungen über Morphium-Alkaloide|journal = Chemische Berichte|year = 1914|volume = 47|issue = 2|pages = 2312–2330|doi = 10.1002/cber.191404702149|url = https://zenodo.org/record/1426553}}</ref> and was used as a cough suppressant and ]. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of ], where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of ] and is metabolised in the liver by demethylation and deacetylation to produce ]. |
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Since acetyldihydrocodeine has higher ] than ] and is converted into dihydromorphine rather than ], it can be expected to be more potent and longer-lasting. It also has a higher ] than codeine. Side effects are similar to those of other ] and include ], ] and ]. |
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Although an opioid of low to moderate strength and use in medicine elsewhere in the world, acetyldihydrocodeine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9051 and the one salt in use, acetyldihydrocodeine hydrochloride, has a freebase conversion ratio of 0.90. |
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== References == |
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{{reflist}} |
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{{Cough and cold preparations}} |
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{{Opioidergics}} |
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] |
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] |
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{{respiratory-system-drug-stub}} |
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{{analgesic-stub}} |